Back

150+ Deep Questions to Get to Know Someone

Less small talk. More real talk.

Below are 150 questions, grouped by theme, for getting past the weather and the job title. They work on a first date, on a long drive, at dinner with a partner of ten years, or with a friend you thought you already knew.

Three things make them work:

  • Answer first. Lead with your own vulnerability before asking for theirs.
  • Ask one, then follow it. The second question matters more than the first.
  • Let silence sit. Most honest answers arrive a few seconds late.

Easy openers

Start here. These warm the room without feeling like an interview, and they give you something real to follow up on.

  1. What's been the best part of your week?
  2. What did you believe about adult life that turned out to be wrong?
  3. What's something you've changed your mind about recently?
  4. What are you slightly obsessed with right now?
  5. What's a compliment you never forgot?
  6. How do you usually spend a Sunday?
  7. What's the last thing that made you laugh out loud?
  8. Where do you feel most like yourself?
  9. What's something small that instantly improves your mood?
  10. What's the best advice you've ignored?
  11. What do people misread about you at first?
  12. What are you better at than you let on?
  13. What's your comfort meal?
  14. What did you want to be at age ten?
  15. What's the last new thing you tried?

Childhood and family roots

Where someone comes from explains most of how they love. Go gently, and answer first yourself.

  1. What was your childhood home like?
  2. Who raised you, really?
  3. What did your family never talk about?
  4. What's a family tradition you kept?
  5. What's one you dropped on purpose?
  6. How was affection shown in your house?
  7. What were you praised for as a child?
  8. What were you punished for?
  9. Which parent are you most like?
  10. Which one did you try hardest not to become?
  11. What did you learn about money at home?
  12. What did you learn about conflict at home?
  13. Where did you feel safest as a kid?
  14. What would your ten-year-old self think of you now?
  15. What do you want to pass on from your upbringing?

Identity and values

The questions that tell you whether your lives can actually fit together.

  1. What do you stand for?
  2. What's a belief you hold that most people around you don't?
  3. When did you last change your mind about something important?
  4. What does a good life look like to you?
  5. What are you unwilling to compromise on?
  6. What does integrity mean to you in practice?
  7. Who do you admire and why?
  8. What part of your identity took longest to accept?
  9. What are you still unlearning?
  10. When do you feel most proud of yourself?
  11. What does success mean to you now?
  12. How has that definition changed?
  13. What would you defend even if it cost you?
  14. What's a rule you live by?
  15. What do you want to be known for?

Love and relationships

Ask these when the conversation has already gone somewhere honest. Answer first, then ask.

  1. What does love feel like to you?
  2. How do you know when you're falling for someone?
  3. What makes you feel wanted?
  4. What makes you pull away?
  5. What's your attachment pattern in early dating?
  6. What do you need after an argument?
  7. What does a good apology look like?
  8. What's a deal breaker you'd never bend on?
  9. How do you handle jealousy?
  10. What do you need to feel secure?
  11. What has a partner taught you about yourself?
  12. What do you do when you feel unseen?
  13. What kind of love did you grow up watching?
  14. What would make you leave?
  15. What would make you stay?

Exes and past loves

Not gossip — patterns. How someone talks about their past tells you how they'll talk about you.

  1. What did your last relationship teach you?
  2. What would your exes say you're like to date?
  3. What part of the ending was yours?
  4. What did you forgive?
  5. What did you never get closure on?
  6. What pattern keeps repeating in your relationships?
  7. When did you last feel truly chosen?
  8. How long do you usually take to heal?
  9. What do you still miss about someone?
  10. What did you learn about your own limits?
  11. What have you stopped tolerating?
  12. What do you do differently now?
  13. Who owes you an apology?
  14. Who do you owe one to?
  15. What do you want to leave in the past?

Intimacy and closeness

Consent applies to questions too. Skip anything that doesn't feel right, in either direction.

  1. How do you like to be taken care of?
  2. What makes you feel close to someone?
  3. What's your love language in practice, not theory?
  4. What kind of touch calms you?
  5. How do you ask for what you want?
  6. What's hard to say out loud?
  7. When do you feel most desired?
  8. What kills the mood for you?
  9. How do you talk about boundaries?
  10. What does emotional safety look like to you?
  11. How much alone time do you need?
  12. How do you like to reconnect after distance?
  13. What's the most intimate thing that isn't physical?
  14. What do you want more of?
  15. What do you want less of?

Money and ambition

Awkward early, fatal later. Better to know now.

  1. What does money mean to you?
  2. How would you describe your relationship with money?
  3. What's your first memory of money?
  4. Do you save or spend by instinct?
  5. What do you happily overspend on?
  6. What does enough look like for you?
  7. How much does work define you?
  8. Would you move country for a job?
  9. What's the most ambitious thing you want?
  10. What are you working toward right now?
  11. How do you feel about a partner earning much more?
  12. How about much less?
  13. Would you split finances or share them?
  14. What's a financial mistake you learned from?
  15. What would you do with a year off?

Dreams and fears

The fastest way past small talk is to admit something first.

  1. What are you most afraid of right now?
  2. What's a dream you haven't said out loud?
  3. What are you avoiding?
  4. What would you do if you couldn't fail?
  5. What keeps you up at night?
  6. What's the bravest thing you've done?
  7. What risk are you glad you took?
  8. What risk do you regret not taking?
  9. What would you regret at eighty?
  10. What do you need to feel brave?
  11. What's the hardest thing you've survived?
  12. What are you hopeful about?
  13. What does your ideal ordinary Tuesday look like in five years?
  14. Who do you want beside you in it?
  15. What are you building toward?

Mental health and self-knowledge

Ask with care. These build trust fast when the answer is met without flinching.

  1. How do you know when you're not okay?
  2. What does your stress look like from the outside?
  3. How do you recharge?
  4. What do you do on a bad day?
  5. Who do you call first?
  6. What helps when you're overwhelmed?
  7. What's your relationship with therapy?
  8. What's a hard season that changed you?
  9. How do you talk to yourself when you fail?
  10. What do you need from a partner on a low day?
  11. What's something you're working on?
  12. What do you need to hear more often?
  13. How do you set boundaries?
  14. What drains you fastest?
  15. What makes you feel steady?

Future, parenting and legacy

Best asked once you know you like each other — and long before you're attached.

  1. Do you want children?
  2. What kind of parent do you think you'd be?
  3. What would you do differently from your parents?
  4. Where do you want to live long term?
  5. What does home mean to you?
  6. How do you imagine a Saturday in ten years?
  7. What do you want your friendships to look like at fifty?
  8. What do you want to have built?
  9. What do you want people to say about you?
  10. How do you want to be remembered by the people closest to you?
  11. What tradition would you start?
  12. What do you want to teach someone?
  13. What would a full life include?
  14. What's still on your list?
  15. What are you no longer chasing?

How to use these on a real date

Don't run the list. Pick one theme for the night and stay in it — jumping from childhood to money to sex in ten minutes feels like a survey, not a conversation.

If a question lands badly, say so and move on. Consent applies to questions too. And if an answer surprises you, resist the urge to fix it; ask what it was like instead.

Get 500+ of these as cards

Bona Dating turns questions like these into a swipeable deck of 500+ prompts across fifteen themes. You can save the ones you love, write down your own answers, and keep a profile for each person you're dating with what they said.

Try the cards free or see lifetime access.